Microscale surface structures have been widely explored as a promising tool for antifreezing or frost avoidance on heat transfer surfaces. Despite studies of many surface feature designs, the mechanisms associated with condensation freezing and ice propagation on microstructured surfaces have yet to be thoroughly elucidated, espectially when it comes to quantitative understanding. In this work, condensation freezing on circular micropillar surfaces is investigated, with varying pillar spacing and height (layout/microscale roughness) but a constant pillar diameter. The pillar layout is found to have significant effects on both liquid nucleation and neighboring droplet interactions, as reflected by the condensation droplet distribution prior to soilidification and eventually the freezing front propagation area velocity. In general, nucleation is preferred on the pillar top rather than the bottom of the pillared surface unless there is a large distance between the pillars. Interactions between neighboring droplets solely on pillar tops (or bottom surfaces) can induce heterogeneity in the droplet distribution and slow freezing front propagation. Based on the roles the pillars play in nucleation, droplet coalescence, and ice bridging, four different condensation states are identified and related to the layout of the pillars, and the freezing front area propagation velocity is found to be different in each state. The findings provide a quantitative basis for designing antifreezing surfaces, applicable to a wide range of thermal systems.